Triethylamine → 5-(4-Fluoro-phenoxy)-6-(1-methanesulfonyl-pyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazole

HRID 13280

Reaction equation

HRID 13280 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]1[CH:40]=[CH:39][C:17]([O:18][C:19]2[C:33]([CH:34]3[CH2:38][CH2:37][CH2:36][NH:35]3)=[CH:32][C:22]3[NH:23][C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[N:25][C:21]=3[CH:20]=2)=[CH:16][CH:15]=1>C(OCC)(=O)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][C:19]2[C:33]([CH:34]3[CH2:38][CH2:37][CH2:36][N:35]3[S:9]([CH3:8])(=[O:11])=[O:10])=[CH:32][C:22]3[NH:23][C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[N:25][C:21]=3[CH:20]=2)=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 231455755-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 231455565-(4-Fluoro-phenoxy)-6-(1-methanesulfonyl-pyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.01 ml of triethylamine and 0.005 ml of methanesulfonyl chloride were added in order to an ethyl acetate (1 ml) solution of 20 mg of 5-(4-fluoro-phenoxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole obtained in Example 168, and the reaction liquid was stirred overnight at room temperature. The reaction solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction solvent was evaporated away under reduced pressure
  3. customthe resulting residue was purified
  4. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-723885e8e8d842f0956be8a09d9fef6e
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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